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    Whiskey Business - Holly Jolly Pop-up!

    3.4 (436 reviews)

    Whiskey Business - Holly Jolly Pop-up! Photos

    WHISKEY BUSINESS - HOLLY JOLLY POP-UP! ATMOSPHERE

    What's the vibe?
    Casual
    DJ
    Moderate noise
    Good for dancing

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    Recommended Reviews - Whiskey Business - Holly Jolly Pop-up!

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    Katie C.

    If you're looking for that summer vibe this is definitely the bar for you. Their outdoor seating has lots of sunshine and umbrellas for coverage. Ordering is super easy - with the simple scan of a barcode you can have everything delivered straight to your table. We still had our waitress check in on us periodically to make sure all of our food/drinks were coming out. There's lots of activities to do in the outdoor area as well. They had a cute unicorn spray water, connect four and a big jenga. There are a ton of drinks on the menu - I was surprised to see my favorite the 'dirty Shirley'. The food was also super delicious. Hands down one of the best experiences.

    Breakfast sandwich
    Mirella K.

    It was my first time at Whiskey Business and I had a lot of fun! My friends and I reserved a little ski chalet room specially made for the holiday season for our friend's birthday brunch. Whiskey Business has 2 floors with a rooftop patio that's vibrant and cute! The ski chalet we reserved was on the rooftop. Reserving the ski chalet was $65 and it was so worth it - it was super cute, warm, and we truly felt like we were at a ski lodge. It was perfect for the holiday/winter season. It wasn't busy even though it was brunch time on a Saturday (thank goodness)! Our food was reallyyyyy yummy - we got the avocado toast, buffalo soldier fries, and breakfast sandwich. Everyone loved their meals and the prices were super affordable, too! Our cocktails were alright, they were pretty small and nothing too special. Our server was alright too, she wasn't really friendly and seemed annoyed we were asking questions about some food items on the menu. Whiskey Business is a great place for food and drinks with friends. It has a fun atmosphere and is surrounded by other restaurants and bars in Wicker Park. I'd for sure come again!

    Chicken and waffles
    Emma S.

    Great rooftop with really fun 80s neon decor (big fan of anything neon). As you'd except, they have good whiskey based drinks, as well as many other cocktails. The brunch platters were delicious- the French toast and chicken are must try's! Looks like they do outdoor movie events during the summer, and have a decent number of TVs to catch any sporting event that happens to be on. Even when raining the rooftop is a great hangout spot

    Pickle backs!
    Thuy Dan T.

    Whiskey business has a nice patio rooftop for you to enjoy with an adjacent indoor bar if you'd like to sit inside. The staff is friendly and there's something at the top looking for an open table for you. There are servers throughout but if you sit inside the bar, you just walk up. If you'd like one of the bigger tables, I'd recommend calling ahead to make a reservation. When sitting in the patio is definitely gets hot under the sun! Not as many fans or misters and the umbrellas are a hit or miss. The frozen drinks are pretty sweet (too much for me). We ordered Jameson shots with pickle backs and the shots were plentiful but the pickle juice was so pretty small. We kept having to ask them to pour more. All in all, a positive experience and I would consider coming back when I'm in the area!

    Latrice A.

    Busy here on Thursday which we learned was ladies nite, hey cool I was with my gal pals I believe we Arrived at 6:00 p.m. close so there was no crowd or no wait to be seated and we were able to seat ourselves and the waiter who was very overwhelmed because he let us know that they were under staff but he did a great job he seemed like to Anticipate when we needed him eated him also I ordered a drink that I was not fond of and the and he swapped it out for me even though I took a couple of sips And we only went with appetizers which was the spinach dip and a quaso nachos It was nice casual vibe it was starting to get crowded as we left

    Mimosa Brunch
    Joneice B.

    Partied here on a Sunday morning with my friend who had reservations for brunch with her cousins. I didn't end up eating here because I had reservations at another location. I will say that they're mimosa deal seem like a really good bargain. I enjoyed my momosa which was made with Wyclif champagne or maybe that's Proseco not sure. My friend got some wings and those looked delicious and they also smell like they had the right level of spice. The outside roof deck had lots of space and a good amount of locations to take some cool pictures. I definitely will come back when I want some good wings and some whiskey.

    Rie U.

    First things first, the rooftop patio is a nice little space for hanging out with friends. There are umbrellas so a little drizzle or sun won't ruin your visit. There are couches for bigger parties, and TVs all around if you're the kinda person who can't miss a game. The food was solid. Didn't blow my mind but also didn't underwhelm me. The chicken and waffles is a smaller dish, which turned out perfectly for me. Totally needed all the deep-fried foods! The Truffle Shuffle Fries were tasty and I'd get that one again! Lastly, 18% gratuity that's automatically added to your bill?? I'm sorry but that's kinda crappy. Also, the electronic billing system doesn't tell you that you've already had 18% added to your bill and it prompts to you add a tip. Wtf? That's some shady business practice imho.

    Inside bar area
    Elizabeth A.

    Came in for a quick drink while waiting for a dinner reservation nearby. The environment inside was really chill and welcoming. The drinks were well priced and yummy. We paid around $50 for 4 drinks and a shot. We tried the spicy mango margarita, paloma, mojito and espresso martini. All four drinks we recommended and would get again. There is also games to play like darts, skeeball, jumbo connect4 and jumbo jenga. The man serving us was also very nice and personable. Definitely looking forward to coming back and checking out the rooftop next time!

    Ashten W.

    We hosted a collaboration event with Guaranteed Karma (a company that rewards volunteers for their altruism) and Whiskey Business on a summertime Chi Saturday afternoon. They were so fun to host an event with. The staff is super welcoming, hospitable, and friendly! After spending an hour street cleaning with the crew, we enjoyed cocktails and delicious shareable bites perfect to share with a large group! If you're visiting Chicago or live in the neighborhood, it's the perfect spot to create good memories with ya friends.

    Rooftop patio
    Brian T.

    Gorgeous rooftop bar during the warm weather. And I believe during certain days they show specific movies. Prices for cocktails are about the usual and they offer bar food until late. Games typically first come first serve include giant connect four and giant Tetris among others

    Chesley M.

    It's always the rooftop for me. I'm a sucker for a good rooftop and Whiskey Business certainly passed the test. This was last summer and sorry it took me so long to review. The happy hour specials are great. It's nice to just chill on a hot summer day. Everyone who works here is simply amazing when it comes to hospitality. I've been here twice since last summer and unfortunately didn't get videos and these were all I had in my camera roll. This is a summer time Chi must. Great for a hangout spot after work or hanging with friends. They' even have rooftop movie night. There is plenty of (paid) street parking. Keep in mind I'm a Bourbon girl so the name alone made me want to check this spot out. Glad I did. Looking forward to our next outing ;).

    Rooftop
    Nick S.

    First time here in the spring on the rooftop. Nice vibe and the staff new what they were doing. Quinn was amazing she new her stuff amd was super friendly.

    Lana T.

    OVERALL: As instagrammable as you think it will be, but it's not just looks! The food, drinks, and overall service make this place a winner. ATMOSPHERE: I mean, I had to start with this one right. A fun rooftop in Wicker Park with fun colorful decor and string lights. They even had a giant inflatable unicorn. They play upbeat pop music that makes you want to dance in your seat. Such fun vibes! DRINKS: They have so many classic drinks like mojitos, old fashions, you name it but our favorites were the (what we called) an adult capri sun and the magic 8 ball shots. The magic 8 ball shots were mystery shots and as you can imagine, you shook a magic 8 ball to figure out your shot. Some options lead to dares and a reroll! FOOD: We ordered the chicken sliders, steak burrito bowl, and Mac and cheese. For a place that we thought might be all looks, typically I don't expect the best BUT this food was absolutely delicious. I would absolutely eat all of these things again. PRICE: I thought the prices here were quite affordable. $10 for Mac and cheese, $8 for the base burrito bowl (we added a protein for $5), and the chicken sliders were $14 for 3 sliders. Drinks ranged from $10-$15. The magic 8 ball shots were $8 each but some of us got some good liquor like Patron. The odds were in our favor that night! SERVICE: Our waitress was extremely attentive and kind. She was super fun to hang out with and encouraged us to video our magic 8 ball shot experience. 10/10 RECOMMEND!

    Frozé

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    6 years ago

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    please email me sonia@cpgrestaurants.com

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    Sonia S.

    Steph, I hope to see you around more!

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    Excellent!!!! Loved it, will definitely be back whenever I'm in town. Day and night vibe was awesome

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    Page 2 of 11

    Ask the Community - Whiskey Business - Holly Jolly Pop-up!

    Are the bottomless mimosas at a specific time? If so when?

    Hi Dena! We do not offer bottomless brunch anymore, however, we have something even better now! It is called the F.O.M.O. - (F***ing Oversized Mimosa Option) Giant Mason Jar… 

    Hello do the haunted cabins have space heaters?

    They are enclosed and have space heaters

    Are the Wednesday movies outside on the rooftop?

    Weather permitting yes they are. Typically between November and March we only feature the movies indoors.

    Are children/people under 21 able to get in?

    I've never seen children in the establishment before. Might be best to call and double check.

    Is the rooftop open in the winter - even to hang in the cold or do they provide heaters?

    Hey Steph! We have curling courts up on the rooftop :) Check out our Facebook or Instagram for photos! Hope to see you soon!

    Is this establishment kid-friendly for Sat and Sunday brunch?

    Not particularly, it is more of an adult day drinking vibe. They have a DJ, however the music isn't all that loud. The rooftop is more mature and the brunch menu isn't kid friendly. However, personally I enjoy an adult vibe.

    Do you have to be 21 to get in?

    Most nights they have bouncers, but not in the AM for brunch.

    View All 9 Questions

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    The Franklin Room

    The Franklin Room

    4.3
    (633 reviews)
    2.0 mi
    $$$

    The vibes were nice. Lighting wasn't too bright, a dressier atmosphere, and definitely felt like a…read moregood spot for drinks and dinner. Service was fine. Our server was nice and water refills came at the right times. The burger was honestly pretty mid. It tasted fine, but our server said it was one of the best burgers in Chicago and I definitely wouldn't agree. 5/10. The salmon was tender and had a really interesting crust. It wasn't charred like I expected, almost had a rubbery texture, but I actually enjoyed it. The lemony miso sauce was delicious, the pickled cucumbers added a nice crunch. 7.5/10. The prime bone-in ribeye was fine. Good flavor, but nothing really stood out about it. 6.5/10. Dessert was the highlight of the meal. The chocolate crunch dessert was sooo good. Loved the marshmallow pieces and all the different textures from the crunchy mousse. 8/10. The salted caramel gelato had a great texture, but it was way too sweet for me. It tasted more like straight sugar than salted caramel. 6/10. Overall, a solid last-minute date night spot with good vibes, but the chocolate crunch dessert was definitely the standout.

    Instagram sent me, not via an influencer, but a very alluring ad. If I were to book a reservation…read morethen and there, I could get an Old Fashioned made with Colonel E.H. Taylor for a lower price. Sold! I made a reservation and stopped in that week (if not that very day). The Old Fashioned was fantastic! It had strong whiskey notes without hitting you with a wall of spirit the way a Manhattan, for example, does. The other additions of bitters and syrup did a perfect job rounding the cocktail out, adding sweet and savory notes. As much as I love variety, I loved it so much, I ordered two! I can't lie and say this wasn't at least in part due to the reduced price, that notwithstanding, me ordering two of the same is some of the highest, non-verbal praise one could get from me. For a main, I had the opportunity to try the burger, a special only available 5:00 - 6:30, and mind you I eked in by the skin of my teeth. Before I attempt to break this down, though, I need to take a slight tangent: Do any of you remember the quote from The Menu where Anya Taylor-Joy says: "A real cheeseburger. Not some fancy, deconstructed, affluent b***s***, a *real* cheeseburger."? I am pleased to report the burger here was somewhere between Chef Slowik's "very traditional cheeseburger" and the one Taylor Joy describes! In other words, just fancy enough to feel like I am getting a unique, creative, well thought out dish, but without all the pomp and circumstance! There's just one little problem: as soon as I bit into it, the juices erupting from within soaked the bottom bun, and turned it into a fork and knife affair with an unseen level of precision and speed. Very regrettably, this was the burger's undoing. That first, heavenly bite that had angels singing showed what the burger was really made of (and I mean this figuratively and literally). The beef was of the highest quality, well-seasoned, cooked medium and juicy, with a perfect sear that would have Louis Camille Maillard crying tears of joy. Two types of cheese (one being crisp and airy, the other thoroughly gooey and savory), the perfect amount of bacon, moisture and flavor from a tempura tomato, and divine sauces! One of them was a little sweet, which elevated the flavor like no one's business. Together, all these flavors were a symphony that could give Beethoven a run for his money. However, that unfortunate fact that the thing fell apart so quickly meant that symphony was limited to one bite, the rest being encountered piecemeal. I would rather skip fries than skip dessert (which I did), and ordered the Mango cheesecake. Such velvety perfection! Neither the sweetness nor the mango notes were overpowering, and while it didn't have the crust of a traditional cheesecake, the more gentle variant here absolutely works. I also appreciated the tart sorbet to offer some contrast in flavor, temperature, and texture. Now, let me talk about the service. Given that the restaurant was at capacity, the bar service and speed to get my items was reasonable. Could it hypothetically have been just a touch faster/more attentive? Yes, but in practice, when you have a full house, this is as good as it can get before robots take over. Finally, there is the matter of prices. There is no doubt in my mind that the quality is up there, at the same time, the reason I skipped the side of fries was it would have set me back $11. I suppose the real question is whether or not the quality equals the price, and after some reflection, I think the answer is yes, but one must be prepared for the sticker shock ahead of time. That said, the final verdict: The Franklin Room absolutely delivers on an all-around fantastic meal. I think whatever you order will be in the 90th percentile, at worst! However, this comes at a cost. Therefore, I would love to return to the Franklin Room, but it would likely be more a very occasional treat than a place where I'd be a regular.

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    The Franklin Room
    Mango Cheese Cake
    Mango Cheese Cake
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    The Berkshire Room

    The Berkshire Room

    4.1
    (475 reviews)
    2.5 mi
    $$

    The Berkshire Room is one of my favorite speakeasies in Chicago. While they offer a fantastic…read morecocktail menu and a full bar, I almost always order The Dealer's Choice. You simply choose your preferred spirit, flavor profile, and glassware, then let the mixologist create something just for you. It's one of my favorite cocktail experiences in the city, and they've never steered me wrong. What I especially appreciate is how knowledgeable the bartenders are. They're always happy to offer recommendations if you're unsure what to order, but they're equally excited to create something completely unique if you're feeling adventurous. Watching them craft each drink is part of the experience. I've even hosted a birthday gathering here in their private side room, where we enjoyed charcuterie boards alongside our cocktails. If you're just stopping in for drinks, though, I'd recommend grabbing dinner beforehand, as the food offerings are fairly limited. More often than not though, you'll find me sitting right at the bar. I love watching the bartenders showcase their craft and chatting with them about the incredible selection of spirits they have on hand. It's a great spot for anyone who genuinely appreciates well-made cocktails and the artistry behind them. I'm also a member of their loyalty program, which is well worth joining. It can be used at The Berkshire Room as well as several other excellent restaurants, making it an easy way to earn rewards while exploring some great dining spots around the city. Whether you're a cocktail enthusiast or simply looking for a sophisticated place to unwind, The Berkshire Room consistently delivers. I'll definitely be back for another Dealer's Choice soon! #YelpEliteSquad

    I added a photo and was surprised to see I've never reviewed this popular cocktail spot. I've been…read morea handful of times over the years, as it's a solid standby in River North. Tucked away in the Acme hotel, the vibe is loungey with plenty of different types of seating. We came around midnight on a Friday and it was packed but we managed to find a cozy corner. For drinks, I've always enjoyed their "Dealer's Choice", which is a fun novelty. However, on my latest visit I decided to try the Frijolito ($18), which was basically a spin on an espresso martini but with mezcal. Wow! Perfectly balanced, unique, and delicious. For food, they offer some "bites" but I've not tried them. Our server was fine, nothing special. I can't remember ever having bad service here.

    Photos
    Trust the mixologist - your Dealer's Choice cocktail is in good hands
    Trust the mixologist - your Dealer's Choice cocktail is in good hands
    Host your next event at this speakeasy cocktail and whiskey bar in River North!
    Host your next event at this speakeasy cocktail and whiskey bar in River North!
    Bar

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    The Office

    The Office

    4.3
    (320 reviews)
    1.7 mi
    $$$$

    I really like the office! Cool, cozy, and classic! Service is spectacular of course. Always treated…read morewell. The cocktails are also classic but still modern and very cool. Always a nice spot to go back to.

    The Office is a nice speakeasy! I had wanted to get a floral drink at the restaurant upstairs…read morecalled "the Aviary" but they were actually totally full, whereas the speakeasy wasn't. I sat at the bar downstairs and can confirm the place has a classic speakeasy feel -- the the basement of a place behind a locked door, very dark inside with mood lighting/glass cases and leather chairs/couches around small low tables. It's definitely a great date spot! I took off a star because it's pricey -- I got the "milk punch" on their classic cocktail menu which was $25 and is pretty small, but it's a nice drink and tasted very much like a milk punch drink I got at a speakeasy back home (in Austin, TX). The bartenders were super nice and provided excellent service, no complaints there! The bathrooms were also immaculate. Overall, this is a very nice speakeasy! I've been to many in my day and the ambiance is definitely on par with the best, but I gotta say some other unique ingredients (ideally more floral options!) would really take their menu up a notch! Nevertheless, I would def rec a visit to those visiting Chicago, and would go again even just for vibes :)

    Photos
    Twas a combination of a black manhattan & a vieux carré  Delicious
    Twas a combination of a black manhattan & a vieux carré Delicious
    Basque cheesecake was delicious
    Basque cheesecake was delicious
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    Whiskey Business - Holly Jolly Pop-up! - whiskeybars - Updated August 2026

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